"Error: sending the request failed" trying to perform OTA DFU with nRF Connect app

I am on nRF Connect 2.5.0 SDK. I am trying to add OTA DFU support to my custom board using the MCUBoot bootloader, and everything appears normal when I look at the characteristic table but when trying to upload to the device using the nRF Connect app on iOS, the app appears to slowly upload the firmware (displaying low upload speed ~0.5kbps) then after a few minutes gives me "Error: sending the request failed". My board has no UART connection and I have been using RTT logging using the J-link on an nrf52DK; from what I have seen MCUboot logging with RTT is not reliable, and I have not been able to get it to work either. 

My procedure: 

1. Build and flash MCUboot and app onto the custom board with an nrf52DK.

2. Change my app and build the new app.

3. use nRF Connect app to try to upload 'app_update.bin' to device in upgrade mode "test and confirm". The procedure always fails before completing.

Here is my bootlaoder config in my prj.conf:

 

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# Bootloader Configuration
#==================================
CONFIG_BOOTLOADER_MCUBOOT=y
CONFIG_NCS_SAMPLE_MCUMGR_BT_OTA_DFU=y
CONFIG_MCUBOOT_BOOTLOADER_MODE_SWAP_WITHOUT_SCRATCH=y
CONFIG_MCUBOOT_BOOTLOADER_NO_DOWNGRADE=n
CONFIG_IMG_MANAGER=y
CONFIG_PARTITION_MANAGER_ENABLED=y
# Enable most core commands.
CONFIG_MCUMGR_GRP_IMG=y
CONFIG_MCUMGR_GRP_OS=y
# Enable mcumgr.
CONFIG_MCUMGR=y
CONFIG_MCUMGR_TRANSPORT_BT=y
CONFIG_MCUMGR_TRANSPORT_BT_AUTHEN=n
# Some command handlers require a large stack.
CONFIG_SYSTEM_WORKQUEUE_STACK_SIZE=3072
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX

Here is my child_image/mcuboot.conf: 

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CONFIG_BOOT_SIGNATURE_TYPE_ECDSA_P256=y
#this is an absolute path, change it yourself
CONFIG_BOOT_SIGNATURE_KEY_FILE="C:/Vitalmark/keys/private.pem"
#reduce mcuboot partition size
CONFIG_PM_PARTITION_SIZE_MCUBOOT=0x10000
# Disable UART Console and enable the RTT console
CONFIG_UART_CONSOLE=n
CONFIG_RTT_CONSOLE=y
CONFIG_USE_SEGGER_RTT=y
# Config logger
CONFIG_LOG_BACKEND_RTT=y
CONFIG_LOG_BACKEND_UART=n
CONFIG_MULTITHREADING=y
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX

and I have also statically defined the flash partitions in pm_static.yml based on the first automatically partitioned build:

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app:
address: 0x10200
end_address: 0x48000
region: flash_primary
size: 0x37e00
mcuboot:
address: 0x0
end_address: 0x10000
placement:
before:
- mcuboot_primary
region: flash_primary
size: 0x10000
mcuboot_pad:
address: 0x10000
end_address: 0x10200
placement:
align:
start: 0x1000
before:
- mcuboot_primary_app
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX

Here is the log from the nrf connect app: 

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Scanner On.
Device Scanned.
Device Appearance switched from Generic to UART.
Connected.
Discovered Nordic UART Service, 0483DADD-6C9D-6CA9-5D41-03AD4FFF4ABB, and SMP Service Services.
Discovered Characteristics UART TX Characteristic and UART RX Characteristic for Service Nordic UART Service.
Discovered Characteristics 1524 for Service 0483DADD-6C9D-6CA9-5D41-03AD4FFF4ABB.
Discovered Characteristics SMP Characteristic for Service SMP Service.
Discovered Client Characteristic Configuration for Characteristic UART TX Characteristic
Characteristic UART RX Characteristic has no Descriptors.
Characteristic 1524 has no Descriptors.
Device Appearance switched from UART to McuMgrDFU.
Discovered Client Characteristic Configuration for Characteristic SMP Characteristic
Found valid Firmware in file:///var/mobile/Containers/Data/Application/4D4197EB-C6BC-4ECA-861F-10957E6527CB/Library/Caches/app_updateAF08E5E7-D04E-4537-986B-CAA02FF5CA2D-95620-00001C3F1CF8B74E.bin for Device DFU McuMgr.
Central Manager ready
Peripheral connected
Device ready
LIST Command Performed with Success.
Upgrade started with 1 image(s) using 'Test and Confirm' mode
Firmware Upgrade Started.
State changed from none to requestMcuMgrParameters
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX

I am fairly certain it is not a connection issue, since I never had any issues with the old NordicDFU on the nrf5 SDK using the exact same board. Since I don't have a UART port for MCUBoot logging I'm not sure how I can diagnose this issue. Any help would be much appreciated